title: Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.
abstract: A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.
authors.affiliation: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, United States.
authors.forename: Jeremy
authors.initials: J
authors.lastname: Kister
authors.forename: Philippe
authors.initials: P
authors.lastname: Nuhant
authors.forename: Ricardo
authors.initials: R
authors.lastname: Lira
authors.forename: Achim
authors.initials: A
authors.lastname: Sorg
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D007700:Kinetics; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C082780:tetrafibricin